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β-Oxo ِAnilides in Heterocyclic Synthesis: Novel Synthesis of Pyridazinones, Pyrazolopyridazines and Cinnolines

Article

Last updated: 01 Jan 2025

Subjects

-

Tags

Organic chemistry

Abstract

Compound 1 coupled smoothly with aromatic diazonium salts to yield the corresponding arylhydrazones 2a-d. Compounds 2a-d condensed with DMF-DMA in refluxing xylene to yield the pyridazinones 3a-d. Compounds 3a-d were also established based on its further reaction with some active methylene reagents and some nucleophilic reagents. So, reactions of 3a, b with malononitrile in refluxing ethanolic piperidine afforded arylidinemalononitrile 4a,b. The pyridazinone derivatives 3a, b reacted with hydrazine hydrate to afford the hydrazine derivatives 5a, b. When 3a,b were fused with hydrazine hydrate without solvent, the pyrazolo[4,3-c]-pyridazines 6a,b were obtained. Compounds 6a, b were also obtained when compounds 5a, b melt over melting point for short time. Condensation of 2a, b with ethyl cyanoacetate yield 7a, b. Similarly, reactions of 2a,b with 1 mole of malononitrile afforded the pyridazine derivatives 8a,b. While, when 2 moles of malononitrile reacted with 2a, b in the same experimental conditions to yield the cinnoline derivative (9a, b). Reactions of pyridazine 8a,b with 1 mole of malononitrile afforded 9. Compound 2b was reacted with a mixture of arylidinemalononitrile and acrylonitrile to yield product formulated as triazole moieties 12a, b. Similarly, compound 2b was reacted with a mixture of maleic anhydride and acrylonitrile in the same above experimental conditions to give 13. Also, reactions of 2b with hydroxylamine hydrochloride yield 14.

DOI

10.21608/ejchem.2018.3901.1343

Keywords

Pyridazinones, dyes, Pyrazolopyridazines, Cinnolines

Authors

First Name

Abdelhaleem

Last Name

Hussein

MiddleName

M

Affiliation

Department of Chemistry, Faculty of Science, Al Azhar University, Assiut 71524, Egypt

Email

abdelhaleemmh@yahoo.com

City

-

Orcid

-

First Name

Mohamed

Last Name

El-Gaby

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Science, Al Azhar University, Assiut 71524, Egypt

Email

m_elgaby@hotmail.com

City

-

Orcid

0000-0002-4902-5546

First Name

Fathi

Last Name

Abushanab

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Science, Al Azhar University, Assiut 71524, Egypt

Email

fathiabushanab@yahoo.com

City

-

Orcid

-

First Name

Mohamed

Last Name

Abdel-Raheim

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Science, Al Azhar University, Assiut 71524, Egypt

Email

sara.morsy@msa.edu.eg

City

-

Orcid

-

First Name

Morsy

Last Name

Elapasery

MiddleName

-

Affiliation

Dyeing, Printing and Auxiliaries Department, Textile Research Division, National Research Centre, Cairo 12622, Egypt

Email

elapaserym@yahoo.com

City

-

Orcid

0000-0002-4686-2007

Volume

61

Article Issue

6

Related Issue

2055

Issue Date

2018-12-01

Receive Date

2018-05-24

Publish Date

2018-12-01

Page Start

1,111

Page End

1,119

Print ISSN

0449-2285

Online ISSN

2357-0245

Link

https://ejchem.journals.ekb.eg/article_10065.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=10065

Order

44

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

β-Oxo ِAnilides in Heterocyclic Synthesis: Novel Synthesis of Pyridazinones, Pyrazolopyridazines and Cinnolines

Details

Type

Article

Created At

22 Jan 2023